Pd‐Senphos Catalyzed <i>trans</i>‐Selective Cyanoboration of 1,3‐Enynes
Yuanzhe Zhang, Bo Li, Shih‐Yuan Liu
Abstract
The first trans-selective cyanoboration reaction of an alkyne, specifically a 1,3-enyne, is described. The reported palladium-catalyzed cyanoboration of 1,3-enynes is site-, regio-, and diastereoselective, and is uniquely enabled by the 1,4-azaborine-based Senphos ligand structure. Tetra-substituted alkenyl nitriles are obtained providing useful boron-dienenitrile building blocks that can be further functionalized. The utility of our method has been demonstrated with the synthesis of Satigrel, an anti-platelet aggregating agent.
Topics & Concepts
EnyneAlkyneCatalysisChemistryPalladiumCombinatorial chemistryLigand (biochemistry)TetraBoronStereochemistryMedicinal chemistryOrganic chemistryReceptorBiochemistryOrganoboron and organosilicon chemistryCatalytic Cross-Coupling ReactionsRadical Photochemical Reactions